I will judge the parent if the name is cruel - for instance when the news story about little Adolf Hitler and his sister JoyceLynn Aryan Nation came out. I judged that the parents were not-very-nice neo-nazis and the kids were in trouble saddled with parents like that. Turns out I was right - the father is a violent neo-nazi and the kids were taken into care and will never be going home.
However I do NOT class names like Chelsea, Cheryl or Sharli to be cruel. They don't have any nasty connotations, there's nothing wrong at all with them as a name. I would never judge a child or parent based on that.
My eldest has a very unusual name and i think it would be classed along with Sharli and Kaidon by the KH's of the world. Not that I'll ever know, no one on ANY of the multitude of name threads on this site has ever mentionned it, ever. But I don't give a damn. I love her name, it grew on me, and it suits her perfectly
My middle one has a name which is a top-50 (or maybe top 20 or 10, not sure) name in other countries but unusual here. Think like 'Jesus' - everyone knows it's a name, and a popular one too, in some countries, but there aren't many born-in-Britain Jesus's.
If asked about either of their names, I just smile and say yes, how my daughter's names are lovely and suit them, and your kids names are also lovely by the way...stops the conversation every time.